hydrogenchloride 0.25 h; boiling water bath;

in ethanol 2 h; on the boiling water bath; Yield given;

triethylamine in toluene 1 h; Heating;

1: 100 percent / H2 / Raney nickel / ethanol / 760 Torr / Ambient temperature 2: ethanol / 2 h / on the boiling water bath View Scheme

1: 82 percent / hydrochloric acid, sodium nitrite, sodium acetate / H2O 2: 100 percent / H2 / Raney nickel / ethanol / 760 Torr / Ambient temperature 3: ethanol / 2 h / on the boiling water bath View Scheme